Absolute configuration of the 5,6-oxide formed from 7,12-dimethylbenz[a]anthracene by cytochrome P450c |
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| Authors: | S K Balani H J Yeh D E Ryan P E Thomas W Levin D M Jerina |
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| Affiliation: | 1. Center for Community Progress, 1001 Connecticut Avenue NW Suite 1235, Washington, DC 20036, USA;2. Helmholtz Centre for Environmental Research – UFZ, Department of Urban and Environmental Sociology, Permoserstr. 15, 04318 Leipzig, Germany;3. Meijigakuin University, Faculty of Economics, 1-2-37 Shiroganedai, Minato-ku, Tokyo 1520023, Japan;1. University of Auckland, New Zealand;2. Deakin University, Australia;3. Flinders University, Australia;4. Turning Point, Melbourne, Australia;5. Monash University, Australia;6. University of Melbourne, Australia |
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| Abstract: | The absolute configurations of the enantiomeric 5,6-arene oxides of 7,12-dimethylbenz[a]anthracene (DMBA) were recently assigned such that the late eluting enantiomer from a chiral HPLC column has 5R,6S absolute configuration. [Mushtaq et al. (1984) BBRC 125, 539]. The authors further concluded that the 5R,6S-enantiomer predominates on metabolism of DMBA by cytochrome P450c in liver microsomes from 3-methylcholanthrene-treated rats. Their chemical assignment of absolute configuration is incorrect. Thus, metabolism of DMBA by these microsomes as well as by homogeneous cytochrome P450c produces 5,6-oxide highly enriched (95%) in the 5S,6R-enantiomer in accord with theoretical predictions. |
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